Hexamethyldisilazane → HCID 70162033, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.92 ml of hexamethyldisilazane in 2.5 ml of THF is treated dropwise at 0° C. with 2.63 ml of 1.6M butyl-lithium in hexane. After 15 min. the mixture is cooled to -78° C. and 0.6g (Ex. Fa) of (E)-1-[4-[4-(allyl-methyl-amino)-but-2-enyloxy]-3-fluorophenyl]-ethanone (Ha) in 1.9 ml of THF is added dropwise. After 1 hr. at -78° C. 0.5 ml of geranyl bromide in 1 ml of THF is added dropwise. The mixture is left to warm to room temperature, stirred for 1 hr. and poured into saturated sodium bicarbonate solution/ether. The organic phase is washed with 10% sodium chloride solution, dried and evaporated. After silica gel chromatography with (97.5%) methylene chloride/methanol the residue is dissolved in ethanol with 0.87 g of fumaric acid, evaporated and precipitated from ether with pentane. There is obtained 0.24 g of (E)-1-[4-[(E)-4-(allyl-methyl-amino)-but-2-enyloxy]-3-fluoro-phenyl]-2-[(E)-3,7-dimethyl-octa-2,6-dienyl]-5,9-dimethyl-deca-4,8-dien-1-one.fumarate (1:2), MS: m/e 549 (M).

Provenance & Evidence